Process for preparing a phosphinoalkanol

Abstract

The present invention is generally directed to electroluminescent Ir(III) compounds with phosphinoalkoxides and phenylpyridines or phenylpyrimidines, and devices that are made with the Ir(III) compounds.

1. A process of preparing a phosphinoslkanol comprising:
 (1) combining an epoxide with aqueous HBr, to form a bromohydrin; 
 (2) isolating the bromohydrin from step (1) and removing water; 
 (3) combining the dried bromohydrin from step (2) with n-butyl lithium, wherein the molar ratio of n-butyl lithium to the bromohydrin is about 2; 
 (4) adding a chlorophosphine to the product of step (3); and 
 (5) adding acid to the product of step (4). 
 
     
     
       2. The process of  claim 1  wherein the epoxide is 1,1-bis(trifluoromethyl)ethylene oxide. 
     
     
       3. The process of  claim 1  wherein the chlorophosphine is chlorodiphenylphosphine. 
     
     
       4. The process of  claim 1  wherein the phosphioalkanol comprises Formula III-H: 
       
         
           
           
               
               
           
         
       
       wherein
 R 9 can be the same or different at each occurrence and is selected from C m (H+F) 2n+1  and C 6 (H+F) p Y 5−p ; 
 R 10  can be the same or different at each occurrence and is selected from H, F, and C n (H+F) 2n+1 ; 
 Y is C m (H+F) 2m+1 ; 
 n is an integer from 1 through 12; 
 m is 2 or 3; and 
 p is 0 or an integer from 1 through 5. 
 
     
     
       5. The process of  claim 1  wherein the epoxide is substituted with one or more groups selected from alkyl, partially fluorinated alkyl, and perfluorinated alkyl. 
     
     
       6. The process of  claim 1  wherein the epoxide is substituted with trifluoromethyl groups. 
     
     
       7. The process of  claim 1  wherein the chlorophosphine is selected from chlorodialkylphosphine and chlorodiarylphosphine.